Dithiocarbamate

Chemical structure of dithiocarbamates

A dithiocarbamate is a functional group in organic chemistry. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms. Sodium diethyldithiocarbamate is a common example. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.[1]

Formation and reactions

Many primary and secondary amines react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:[1]

R2NH + CS2 + NaOH → R2NCS2−Na+ + H2O

Ammonia reacts with CS2 similarly:

2 NH3 + CS2 → H2NCS2−NH4+

Dithiocarbamate salts are pale colored solid that are soluble in water and polar organic solvents.

Applications

Zinc dithiocarbamates are used to modify the crosslinking of certain polyolefins with sulfur, a process called vulcanization. They are used as ligands for chelating metals.[2]

Dithiocarbamates specifically ethylene bisdithiocarbamates, EBDCs, in the form of complexes with manganese (maneb), zinc (zineb) or a combination of manganese and zinc (mancozeb), have been used extensively as fungicides in agriculture from the 1940s.[3][4]

See also

References

  1. 1 2 Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2
  2. ↑ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0-08-037941-9.
  3. ↑ http://www.apsnet.org/publications/apsnetfeatures/Pages/Fungicides.aspx
  4. ↑ Gullino, Maria Lodovica, et al. "Mancozeb: past, present, and future." Plant Disease 94.9 (2010): 1076-1087.
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